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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (80) Show 80 proteins XML

enzymes (80) Show 80 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-09-12 02:02:36 UTC

Update Date

2021-09-16 15:28:36 UTC

HMDB ID

HMDB0009953

Secondary Accession Numbers

HMDB09953

Metabolite Identification

Common Name

PIP(18:0/18:3(9Z,12Z,15Z))

Description

PIP(18:0/18:3(9Z,12Z,15Z)) is a phosphatidylinositol phosphate. Phosphatidylinositol phosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a phosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol phosphates are generated from phosphatidylinositols, which are phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated. Phosphatidylinositols phosphates can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PIP(18:0/18:3(9Z,12Z,15Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of a-linolenic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil. The most important phosphatidylinositol phosphate in both quantitative and biological terms is phosphatidylinositol 4-phosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. Phosphatidylinositols phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol.

Structure

MOL SDF PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
PIP(18:0/18:3)	Lipid Annotator, HMDB
PIP[3'](18:0/18:3(9Z,12Z,15Z))	Lipid Annotator, HMDB
1-octadecanoyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3'-phosphate)	Lipid Annotator, HMDB
Phosphatidylinositol Phosphate(18:0/18:3)	Lipid Annotator, HMDB
PIP(36:3)	Lipid Annotator, HMDB
1-stearoyl-2-a-linolenoyl-sn-glycero-3-phosphoinositol-phosphate	Lipid Annotator, HMDB
PIP(18:0/18:3(9Z,12Z,15Z))	Lipid Annotator
1-octadecanoyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphoinositol-phosphate	Lipid Annotator, HMDB
Phosphatidylinositol Phosphate(36:3)	Lipid Annotator, HMDB
{[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonate	Generator, HMDB

Chemical Formula

C₄₅H₈₂O₁₆P₂

Average Molecular Weight

941.0705

Monoisotopic Molecular Weight

940.5078096

IUPAC Name

{[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonic acid

Traditional Name

[(1R,5S)-2,3,4,6-tetrahydroxy-5-{[hydroxy(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-(octadecanoyloxy)propoxyphosphoryl]oxy}cyclohexyl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(=O)(O)O)C1O)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC

InChI Identifier

InChI=1S/C45H82O16P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(46)57-35-37(59-39(47)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)36-58-63(55,56)61-45-42(50)40(48)41(49)44(43(45)51)60-62(52,53)54/h6,8,12,14,18,20,37,40-45,48-51H,3-5,7,9-11,13,15-17,19,21-36H2,1-2H3,(H,55,56)(H2,52,53,54)/b8-6-,14-12-,20-18-/t37-,40?,41?,42?,43?,44-,45+/m1/s1

InChI Key

KFWDHEJMINKGBX-CFVBTEIUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycerophosphoinositol phosphates. These are lipids containing a common glycerophosphate skeleton linked to at least one fatty acyl chain and an inositol-5-phosphate moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoinositol phosphates

Direct Parent

Glycerophosphoinositol phosphates

Alternative Parents

Substituents

Glycerophosphoinositol phosphate
Diacylglycerophosphoinositol
Glycerophosphoinositol
Inositol phosphate
Cyclohexanol
Fatty acid ester
Dialkyl phosphate
Monoalkyl phosphate
Cyclitol or derivatives
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Biological location

Organ

Brain

Cellular substructure

Extracellular

Ingestion

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Spectral Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0067 g/L	ALOGPS
logP	10^(6.53) g/L	ALOGPS
logP	10^(9.56) g/L	ChemAxon
logS	10^(-5.2) g/L	ALOGPS
pKa (Strongest Acidic)	1.08	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	256.04 Å²	ChemAxon
Rotatable Bond Count	41	ChemAxon
Refractivity	243.19 m³·mol⁻¹	ChemAxon
Polarizability	104.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

All Tissues
Brain

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24767834

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750489

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Only showing the first 10 proteins. There are 80 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:: PLCB1
Uniprot ID:: Q9NQ66
Molecular weight:: 138565.805

Enzyme Details

2. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-4

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. This form has a role in retina signal transduction.
Gene Name:: PLCB4
Uniprot ID:: Q15147
Molecular weight:: 136105.065

Enzyme Details

3. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-2

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:: PLCB2
Uniprot ID:: Q00722
Molecular weight:: 134023.21

Enzyme Details

4. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-3

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:: PLCB3
Uniprot ID:: Q01970
Molecular weight:: 138797.725

Enzyme Details

5. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-2

General function:: Involved in phosphoinositide phospholipase C activity
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. It is a crucial enzyme in transmembrane signaling.
Gene Name:: PLCG2
Uniprot ID:: P16885
Molecular weight:: 147868.67

Enzyme Details

6. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1

General function:: Involved in calcium ion binding
Specific function:: Mediates the production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). Plays an important role in the regulation of intracellular signaling cascades. Becomes activated in response to ligand-mediated activation of receptor-type tyrosine kinases, such as PDGFRA, PDGFRB, FGFR1, FGFR2, FGFR3 and FGFR4. Plays a role in actin reorganization and cell migration.
Gene Name:: PLCG1
Uniprot ID:: P19174
Molecular weight:: 148658.92

Enzyme Details

7. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. Essential for trophoblast and placental development.
Gene Name:: PLCD1
Uniprot ID:: P51178
Molecular weight:: 88134.23

Enzyme Details

8. N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase

General function:: Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:: Involved in the second step of GPI biosynthesis. De-N-acetylation of N-acetylglucosaminyl-phosphatidylinositol.
Gene Name:: PIGL
Uniprot ID:: Q9Y2B2
Molecular weight:: 28530.965

Enzyme Details

9. Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q

General function:: Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:: Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:: PIGQ
Uniprot ID:: Q9BRB3
Molecular weight:: 65343.25

Enzyme Details

10. Phosphatidylinositol N-acetylglucosaminyltransferase subunit A

General function:: Involved in biosynthetic process
Specific function:: Necessary for the synthesis of N-acetylglucosaminyl-phosphatidylinositol, the very early intermediate in GPI-anchor biosynthesis.
Gene Name:: PIGA
Uniprot ID:: P37287
Molecular weight:: 54126.065

Only showing the first 10 proteins. There are 80 proteins in total.

Show all enzymes and transporters

Showing metabocard for PIP(18:0/18:3(9Z,12Z,15Z)) (HMDB0009953)

MOL for HMDB0009953 (PIP(18:0/18:3(9Z,12Z,15Z)))

3D MOL for HMDB0009953 (PIP(18:0/18:3(9Z,12Z,15Z)))

3D SDF for HMDB0009953 (PIP(18:0/18:3(9Z,12Z,15Z)))

3D-SDF for HMDB0009953 (PIP(18:0/18:3(9Z,12Z,15Z)))

PDB for HMDB0009953 (PIP(18:0/18:3(9Z,12Z,15Z)))

3D PDB for HMDB0009953 (PIP(18:0/18:3(9Z,12Z,15Z)))

SMILES for HMDB0009953 (PIP(18:0/18:3(9Z,12Z,15Z)))

INCHI for HMDB0009953 (PIP(18:0/18:3(9Z,12Z,15Z)))

Structure for HMDB0009953 (PIP(18:0/18:3(9Z,12Z,15Z)))

3D Structure for HMDB0009953 (PIP(18:0/18:3(9Z,12Z,15Z)))

Predicted Kovats Retention Indices

Enzymes